Ethyl ether of salicylo-carbonic acid.



UNITED I STATES PATENT OFFICE.

FRITZ HOFMANN, OF ELBERFELD', GERMANY.-

ETHYL ETHEROF SALICYLO-JCARBONICIACID.

srnorrxoh'rron forming part of Letters I atent 639,174, dated December12; 1899. 7

Application filed 0ctohr'31,1899.'

Tool] whom it mag concern:

Be it known that I, F'RITZ HOFMANN, doctor of philosophy, chemist,residing at Elberfeld, Germany, (assignor'to the FARBEN FABRIKEN or ELBEFE'IJD COMPANY, of New York,) have invented a new-and useful Improvementin the'Man ufac'ture t-Production of a New PharmaceuticallCompound; andI hereby declare the following to be a clearand exact descrip; tionof'myinvention'; V 1

' My invention relates to the production-0f the hitherto-unknown'ethylic' ether of salicylo-carbonie'acid having most probably theformula I I o.co.oo, n, I

'\/ oo.on.

, According to my researches this new com-- I so Obtained possessesagreat therapeutic value. It is capable of forming stable alkaline salts,which are readily soluble in water, and it'c an beemployed in theshapeof one of ?these salts I as a valuable'remedy against rheumatic fever.The doses employed for this purpose are from one-half to one gram.

InIcar'rying out my new process practically I- can proceed, as follows,the parts being by I weight: A mixture of one hundred'and thirtyeightparts of pure'salicylicacid and of two h ndr'edan'd forty-two parts ofdimethylani- 1m isdissolved in benzene. -T0 the solution Y 4o thusobtained, 108.5 parts of the ethylic ether of chloro-carbonic acid,which is likewise dissolyedjn benzene, are added under coolingandLenerget-ically stirring. Stirring is continued until the pungentsmell of the chloro-carbonic other has disappeared. Subsequently thereactionymas's'is acidulated by means of diluted hydrochloricacid whilecontinuously stirrin The watery solution thussolution which contains thenew-ether.

' Letters Patent, 'i's',

sammal'zaassl. (fipeoimena) produced which contains the dimethylanilinhydrochlorate,'is separated from the benzene On evaporating the lattersolution the ethylie ether of salicylo-carbonic acid is obtained intheshape of-a crystalline mass, which is-purified byccrystallizationfrom a rn'ixt are of ether and ligroin. It is thus obtained in the shapeof a white crystalline powder, melting at 95 centigrade, and which isreadily soluble in alcohol, ether, chloroform, and in ,benzene,andisqalso soluble in water. 'The alcoholic soluacid is not coloredviolet' -by'aferric chlorid solution, as'is the' case when, using ferricehlorid andan alcoholic solutionof salicylic acid. The new compoundyields'i n the known manner alkaline salts of th e'geh eral formula:

o.oo.oo,n, I l

, l oooio (X meaning an atom of a monovalent alkali,

such as-sodium, potassium, or the'like,-) which when dry andpulverizedare white powders easily soluble in water. I

Having now described my invention and in what manner the same is tobeperformed, what I claim as new, and desire to secure by Asa newarticle of manufacture the ethylic ether ofs'alicylo-carbonicacid-having most probably the formula:

/kcoou -tiou of the'ethylicether of salicylo-carbonic uble in water, thealcoholic solution bein g not colored Violet by aferricchlorid solutionas is thecasewhen using ferric chlorid and an alcoholic 'solutionofsalicylic acid, and which is capable of forming stable alkaline salts,of exhibiting valuable therapeutic properties, the general formula:substantial] y as hereinbefore described.

- In testimony whereof I have subscribed my ame in the presence of twosubscribing wit- 5 nesses. y

FRITZ HOFMANN. 0o, (alkalL) 1 y Tltnesses: these salts being when dryand pulverized R. E. JAHN,

to white powders easily soluble in waterand OTTO KNIG.

